How to Date a Hoodlum
by Lorraine
Summary: A week after Sookie's wedding, and Rory has decided to stay at home. When Rory finally breaks the news about the kiss, how will Lorelai react? More importantly, how will Dean. R/J.
1. Never Go Swimming in Your Pyjamas

How to Date a Hoodlum  
  
by: Lorraine  
  
Disclaimer: I in no way claim rights to Gilmore Girls or any of the characters.  
  
Summary: A week after Sookie's wedding, and Rory has decided to stay at home. When Rory finally breaks the news about the kiss, how will Lorelai react? More importantly, how will Dean.  
  
Pairing: R/J  
  
  
  
Rule #1: Never Go Swimming in Your Pyjamas  
  
GILMORE HOME - MORNING  
  
"Rory, wake up!" Lorelai screamed from the kitchen.  
  
In the next room Rory jerks awake and immediately starts to scowl, before looking at the clock. A look of pure disgust washes over her face.  
  
"It's eight o'clock in the morning!" She yells back.  
  
"Really? I thought it was seven. This means we must hurry," Lorelai is now opening the door to Rory's room."the early people get the coffee."  
  
"What are you babbling on about? Considering your strange awareness at this time of night, you have consumed at least four healthy doses of coffee. And it's the early bird gets the worm."  
  
"Of course its a worm but who in their right mind would eat a worm, even those gross kids who fried them; makes your stomach turn doesn't it? Come on get up, Luke isn't going to come here and deliver the coffee, no matter how many times I ask him. Come on, I can already feel the coffee withdrawal."  
  
"Luke's? How about Sookie's instead, hmm. You're still avoiding Luke right?"  
  
"Rory, Sookie is on her honeymoon. And no I am not avoiding Luke, he's avoiding me. Now why won't you go to Luke's, you haven't gone in all week. Are you avoiding someone?" When Rory gave no reply Lorelai continued. " What happened? You can tell me."  
  
"I don't want you to get mad."  
  
"Why would I get mad? You didn't go and knock off the local liquor store did you?" Lorelai joked.  
  
"No, but IkissedJess."  
  
"A little slower please."  
  
"I kissed Jess." Rory mumbled before getting out of bed, putting on her sandals and walking out of the back door leaving Lorelai baffled about what had just happened.   
  
Rory is now walking through the town square towards the bridge. Not paying attention to whom she is passing. Unfortunately, the people around her are paying attention, especially Dean. Unbeknown to her, he begins to follow her. Rory also didn't notice the dark haired boy sitting in the middle of the bridge without his shirt before she almost tripped over him.  
  
"Oh, hey Jess."  
  
"Rory."  
  
"What are you doing here?"  
  
"Tanning." Jess answers sarcastically. "I'm just here watching the water, sounds dumb, but it's comforting. The fact that it's kinda remote makes it seem less like living under a microscope."  
  
He too had no idea that Dean was hearing every word being said.  
  
"I always thought the same thing. Whenever Mom and I would get into a fight, this is where I went. When I was 10 I used to pretend no one else but me knew about this place, it made it seem special."  
  
They spend the next few minutes watching the ducks bathe themselves before Jess breaks the silence.  
  
"Why did you do it?"  
  
"Can we talk about something else?"  
  
"I need to know."  
  
"I don't know one second we were talking and the next second I just grabbed you. I knew it was wrong, but for some reason it felt right." Rory says refusing to look at Jess.  
  
"Felt right? How did you come up with that?"  
  
Rory smiles sadly, as if remembering something she doesn't want to.  
  
"For the first time in a relationship that I have been part of - not that we have a relationship - I was near someone who understood me. Nothing was expected, there was no obligation to do something. I was so happy to see you, so I kissed you."  
  
In the background Dean's face is contorted with shock and jealousy, but he still stands in the shadows.  
  
Up close Jess is wearing a fleeting smile.  
  
"I don't understand you, I mean the coffee addiction, what's up with that?" Jess retorts trying to make Rory smile and succeeds.  
  
"I don't need to explain things, sometimes I don't even need to speak. Like I said before, it's not obligational. You understand."  
  
Again, they lapsed into a companionable silence. Only disturbed when Rory took off her sandals and skimmed her toes in the water before laying down. Jess soon followed. And again the silence was broken, this time by Jess.  
  
"Was it a mistake?" When getting no response, he turns on his side to face Rory.  
  
"I don't know. I know I should regret it, but I don't." Rory says to no one, sounding confused. She hesitated a moment before turning her head towards Jess.  
  
Slowly Jess sat up and leaned towards Rory, putting his arms on either side of her body before gently leaning down to kiss her. To Jess's surprise Rory didn't pull away, in fact she wound her arms around his neck and pulled him in, to deepen the kiss. Jess then proceeded to slowly trail his tongue along Rory's lower lip asking for the entrance she happily granted him. It wasn't until Lorelai came running that they separated.  
  
Still in a state of shock of what she had just witnessed, Lorelai attempted to form an intelligent sentence.  
  
"Wha- what is going on, when did this happen, why, what?"  
  
"Mom -"  
  
"Wait, let me think about this first," it was a few seconds before Lorelai gained her composure and began questioning the teens, "Before you ran out of the house you said that you kissed Jess, when did that happen?"  
  
"Sookie's wedding," Rory answered, "right after Dad left to answer his phone."  
  
"OK, now are you still with Dean?"  
  
"Yes, only not for long."  
  
"Why, other than the obvious."  
  
"We've been drifting apart for a while now. And the fact that he didn't trust me - before this started that is."  
  
"Are you happy?"  
  
"With Jess, honestly, yes. Dean, not really. We don't have any even remotely similar interests except for eating."  
  
After this revelation, Lorelai looks torn between shock and anger. In the background Dean is displaying the latter.  
  
"I need to do something about you walking out this morning, you know, take a leaf out of the Dane's Book of Punishment."  
  
Lorelai grins evilly as Rory looks on questioningly and Jess already understands what is about to happen. Without letting the phrase sink in Lorelai pushes Jess and Rory into the duck pond.  
  
"What did you do that for?" Rory demanded.  
  
"I already said why. Meet me in the diner in 10 minutes. Maybe you can persuade Jess to let you borrow something."  
  
Lorelai then proceeds to walk across the bridge to Luke's to see if she can beg him to give her coffee. She also doesn't notice Dean hiding in the bushes.  
  
Back in the pond, Rory is still in a state of shock.  
  
"My mother just pushed me into a pond. A duck pond for that matter, in my pyjamas!"  
  
What Rory didn't hear was Jess gliding towards her, in fact she forgot he was there until he snaked his arms around her waist.  
  
"Cute pj's. Come on, lets go get coffee."  
  
Reluctant to let go of Jess, Rory grabbed his hand and pulled him towards the shore. Once out of the water, Rory for the first time that day is embarrassed about her appearance, and self-consciously crosses her arms in front of her.  
  
"Hey, since when have you been modest?"  
  
"Since always." Rory answers matter-of-factly.  
  
"Huh."  
  
"What now?"  
  
"Modest people don't tend to just grab others and kiss them."  
  
"Yeah well....I may have done that but you won't be seeing me naked."  
  
"We'll see about that." Smirks Jess making Rory blush. "Come on, I wanna see what you look like in my Tool shirt." And with that closing remark he put his arm around her waist and started dragging her towards the diner. Out of the corner of his eye Jess sees movement in the bushes, but when he turns his head everything in sight is either a tree or patches of grass.  
  
On the way to the diner several pedestrians noticed Rory and Jess in their embrace; not ten seconds after the couple passed, did those who loved to gossip, namely Miss Patty and Kirk pull out their cell phones and call all of their friends to inform them of Stars Hollow's newest scandal, which in their opinion could easily rival Nixon and his evolvement in Watergate. Either that or the time Bootsy set his pants on fire and ran screaming through the streets- with out them.  
  
  
  
(Lorelai GOING TO THE DINER)  
  
Lorelai is walking to the diner, and appears to be in deep thought. Upon entering the diner she notices Luke and his haste to serve all of his customers. Quietly sitting down at the counter she waits for Luke to take her order.  
  
"What's with you? Your never this quiet at this time in the morning. Actually when you are desperately sleep deprived or are having a bad hair day, you can also be very loud on those days."  
  
"Nothing, umm....can I talk to you for a few minutes? In private?"  
  
"Yeah....sure. Cesar? I'll be right back."  
  
Luke then points to the stairs and follows Lorelai up. "What do you have to say to me?"  
  
"It's about Jess and Rory."  
  
"You now what Lorelai? I'm not getting into-"  
  
"No listen," Lorelai waits for Luke to protest, when he says nothing she continues, "I'm not here to complain I'm here to explain."  
  
"Explain what?"  
  
"Seems like Jess and Rory are going to be dating, no matter how much I bitch and moan."  
  
Luke is speechless.  
  
"I just thought you would like to know." Lorelai says before taking a step toward the door.  
  
"You're going to be o-kay with this?"  
  
"Eventually." And with that Lorelai goes down the stairs into the diner.  
  
Behind her, for the first time since their fight, Luke has a genuine smile on his face.  
  
~ ~  
  
Authors Note: Thanks for reading this far. Make sure to review so I know someone is reading. Constructive criticism is welcome and needed. Should I keep going or is this idea hopeless? 


	2. Bad Grammar Gets You Nowhere

Authors Note: Thank you so much for all the great reviews! I'm not really good when it comes to writing long chapters, but since they are all short, I hope to update more often.  
  
BTW: dancing with monkeys no matter how hilarious, has been know to scar said monkeys minds for life. LOL.  
  
~ ~  
  
Rule #2: Bad Grammar Gets You Nowhere  
  
On Lorelai's way down the stairs she meets a sopping wet Rory, and equally drenched Jess.  
  
"What did you do, go swimming in a lake?" Lorelai snickered.  
  
"A duck pond actually." Dead panned Jess.  
  
"Funny, funny diner boy." Rory and Jess heard Lorelai mutter as she continued her way down the stairs.  
  
Rory shrugging toward Jess ran up the remaining steps and almost crashed into Luke. Being the unarticulate person that he is, Luke said a quick apology to Rory before glaring at Jess and followed Lorelai into the diner.  
  
"Come on, I'll get you something to wear." With that, Rory followed Jess into his room.  
  
Looking around, Rory could barely make out the floor. Book, magazines, cloths, CD's, and any other imaginable material littered the ground. Oddly enough, the bed was made. Smirking at Rory's investigative look, Jess draped the black Tool shirt and black boxers over her head.  
  
"Hey! Don't do that, are you trying to kill me in my ripe old age of seventeen?"  
  
"Of course, you should have died ages ago." With that parting remark, Jess grabbed his own set of cloths and walked right out of the room and closed the door.  
  
(5 minutes later in the Diner)  
  
Rory and Jess are walking down the stairs and into the diner. Babette and Miss Patty are sitting by the window. The moment Rory emerges, they turn to face her, secretive smiles already in place.  
  
"Rory, honey, are you alright? I saw you this morning, you seemed preoccupied." Interrogated Miss Patty, tape recording every word being said.  
  
"I'm fine, finest Rory's ever been. Nothing to think about, it's summer, you know. I don't actually but, who knows." At Miss Patty's strange look Rory decided to make it short and sweet, "just had some stuff on my mind." Turning around Rory gave Luke a look, clearly asking for a large mug of coffee. Once the steaming cup of heaven was in her hands she immediately relaxed, that is until she noticed Jess staring at her. Blushing, Rory tried to turn away, this only caused Jess to widen his smirk. "Do you know what? I think I'm going to go home and get ready for that....thing I have to do." With those parting words, Rory put down her empty mug and ran out of the diner, leaving many baffled towns people - and her flip flops behind.  
  
~ ~  
  
**If anyone has any ideas for this fic, feel free to post them** 


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